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86386-73-4 molecular structure
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2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol

ChemBase ID: 81
Molecular Formular: C13H12F2N6O
Molecular Mass: 306.2707864
Monoisotopic Mass: 306.10406547
SMILES and InChIs

SMILES:
Fc1c(C(O)(Cn2ncnc2)Cn2ncnc2)ccc(F)c1
Canonical SMILES:
Fc1ccc(c(c1)F)C(Cn1cncn1)(Cn1cncn1)O
InChI:
InChI=1S/C13H12F2N6O/c14-10-1-2-11(12(15)3-10)13(22,4-20-8-16-6-18-20)5-21-9-17-7-19-21/h1-3,6-9,22H,4-5H2
InChIKey:
RFHAOTPXVQNOHP-UHFFFAOYSA-N

Cite this record

CBID:81 http://www.chembase.cn/molecule-81.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol
IUPAC Traditional name
2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol
fluconazole
Brand Name
Biocanol
Biozolene
Diflucan
Elazor
Flucazol
Flucostat
Flukezol
Flunizol
Flusol
Pritenzol
Triflucan
Synonyms
2,4-difluoro-,1-bis(1H-1,2,4-triazol-1-ylmethyl)benzyl alcohol
2-(2,4-difluorophenyl)-1,3-di(1H-1,2,4-triazol-1-yl)propan-2-ol
2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol
α-(2,4-Difluorophenyl)-α-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazol-1-ethanol
1-(2,4-Difluorophenyl)-1,1-bis[(1H-1,2,4-triazol-1-yl)methyl]methanol
Biozolene
Difluconazole
Elazor
Fluconal
Flucostat
Flumycon
Flunazol
Flusol
Fluzon
Triflucan
UK 49858
Zoltec
Fungata
Fluconazole
2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol
Diflucan
Trican
Alfumet
Fluconazole
CAS Number
86386-73-4
MDL Number
MFCD00274549
PubChem SID
46505735
24724485
160963544
PubChem CID
3365

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 12.707209  H Acceptors
H Donor LogD (pH = 5.5) 0.5604975 
LogD (pH = 7.4) 0.56095034  Log P 0.56095827 
Molar Refractivity 97.1995 cm3 Polarizability 26.91871 Å3
Polar Surface Area 81.65 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.58  LOG S -2.34 
Solubility (Water) 1.39e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1 mg/L expand Show data source
DMSO: soluble5 mg/mL expand Show data source
Ethyl Acetate expand Show data source
Methanol expand Show data source
Apperance
powder expand Show data source
White to Off-White Solid expand Show data source
Melting Point
138-140°C expand Show data source
Hydrophobicity(logP)
0.4 expand Show data source
-0.44 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
XZ4810000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
room temp expand Show data source
Target
P450 expand Show data source
Gene Information
human ... CYP1A2(1544) expand Show data source
Mechanism of Action
Inhibitor of fungal cytochrome P450 enzyme 14alpha-demethylase expand Show data source
Purity
≥98% (HPLC) expand Show data source
95% expand Show data source
Grade
certified reference material expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Packaging
pkg of 1 g expand Show data source
Application(s)
Antifungal agent expand Show data source
Effective in single oral dose against vaginal candidiasis expand Show data source
Not active against Aspergillus expand Show data source
Prophylactic treatment for AIDS patients expand Show data source
Pharmacopeia Traceability
traceable to USP 1271700 expand Show data source
Empirical Formula (Hill Notation)
C13H12F2N6O expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00196 external link
Item Information
Drug Groups approved
Description Triazole antifungal agent that is used to treat oropharyngeal candidiasis and cryptococcal meningitis in AIDS. [PubChem]
Indication For the treatment of fungal infections.
Pharmacology Fluconazole, a synthetic antifungal agent of the imidazole class, is used to treat vaginal candidiasis. It inhibits the fungal lanosterol 14 alpha-demethylase which thereby prevents the formation of ergosterol which is an essential component in the fungal cell membrane.
Toxicity Symptoms of overdose include hallucinations and paranoid behavior.
Affected Organisms
Fungi
Biotransformation Hepatic
Absorption 90%
Half Life 30 hours (range 20-50 hours)
Protein Binding 11 to 12%
Elimination In normal volunteers, fluconazole is cleared primarily by renal excretion, with approximately 80% of the administered dose appearing in the urine as unchanged drug.
Clearance * 0.23 mL/min/Kg [adults]
* 0.18 mL/min/Kg [In premature newborns within 36 hours of birth]
* 0.22 mL/min/Kg [In premature newborns 6 days old]
* 0.33 mL/min/Kg [In premature newborns 12 days old]
* 0.4 mL/min/kg [9 Months-13 yearsreceiving single-oral 2 mg/kg]
* 0.51 mL/min/Kg [9 Months-13 yearsreceiving single-oral 8 mg/kg]
* 0.49 mL/min/Kg [5-15 yearsreceiving multiple IV 2 mg/kg]
* 0.59 mL/min/Kg [5-15 yearsreceiving multiple IV 4 mg/kg]
* 0.66 mL/min/Kg [5-15 yearsreceiving multiple IV 8 mg/kg]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1331 external link
Research Area: Immunology , Infection
Biological Activity:
Fluconazole is used to treat serious fungal or yeast infections, such as vaginal candidiasis, oropharyngeal candidiasis, esophageal candidiasis, other candida infections, or fungal meningitis. This medicine works by killing the fungus or yeast, or preventing its growth. [1]Fluconazole is also used to prevent candidiasis in patients having bone marrow transplants, who receive cancer or radiation treatment.[1]
MP Biomedicals - 02198986 external link
A highly selective inhibitor of fungal cytochrome P-450 sterol C-14 α-demethylation.
Sigma Aldrich - F8929 external link
Biochem/physiol Actions
Fluconazole is an antifungal agent. It is highly selective inhibitor of fungal cytochrome P-450 sterol C-14 α-demethyllation. Fluconazole is a potent inhibitor of CYP2C9. Fluconazole interferes with fungal ergosterol synthesis and downregulates the metallothionein gene.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. F8929.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Sigma Aldrich - PHR1160 external link
General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.
Biochem/physiol Actions
Fluconazole is an antifungal agent. It is highly selective inhibitor of fungal cytochrome P-450 sterol C-14 α-demethyllation. Fluconazole is a potent inhibitor of CYP2C9. Fluconazole interferes with fungal ergosterol synthesis and downregulates the metallothionein gene.
Toronto Research Chemicals - F421000 external link
Used as an antifungal.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://en.wikipedia.org/wiki/Fluconazole
  • • R.P. Warrell, Jr. and E. Berman, Evaluation of therapeutic efficacy and CNS toxicity in acute refractory leukemia: J. Clin Oncol., 4: 74 (1986).
  • • U.K. Pat., 1982, Pfizer, 2 099 818; CA, 99, 38467q, (synth, pharmacol)
  • • Grant, S.M. et al., Drugs, 1990, 39, 877, (rev)
  • • Cobos Garcia, F.J. et al., Farm. Clin., 1991, 8, 423, (rev)
  • • Morck, H., Pharm. Ztg., 1991, 136, 56; 60, (rev)
  • • Morita, K. et al., Chem. Pharm. Bull., 1992, 40, 1247, (pharmacol)
  • • Fluconazole, (Eds., Powderly, W.G. et al), Marius Press, 1992, (book)
  • • Urbak, S.F. et al., Ophthalmologica, 1994, 208, 147, (use, rev)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 3349, (synonyms)
  • • Goa, K.L. et al., Drugs, 1995, 50, 658, (rev, pharmacokinet)
  • • Pat. Coop. Treaty (WIPO), 1997, Pfizer, 97 28 169; CA, 127, 220800s, (fosfluconazole, synth, pharmacol)
  • • Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 378
  • • Richard, K. et al.: Antimicrob. Ag. Chemother., 27, 832 (1985)
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PATENTS

PATENTS

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